JPS6377878A - 4、5−ジヒドロ−オキサゾ−ルの新規誘導体、その製造方法及びその使用法 - Google Patents
4、5−ジヒドロ−オキサゾ−ルの新規誘導体、その製造方法及びその使用法Info
- Publication number
- JPS6377878A JPS6377878A JP62225453A JP22545387A JPS6377878A JP S6377878 A JPS6377878 A JP S6377878A JP 62225453 A JP62225453 A JP 62225453A JP 22545387 A JP22545387 A JP 22545387A JP S6377878 A JPS6377878 A JP S6377878A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- dihydro
- formulas
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000002496 gastric effect Effects 0.000 abstract description 2
- 108091006112 ATPases Proteins 0.000 abstract 1
- 102000057290 Adenosine Triphosphatases Human genes 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 230000028327 secretion Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- -1 methoxy, ethoxy, propyloxy Chemical group 0.000 description 6
- 150000002460 imidazoles Chemical class 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZABMHLDQFJHDSC-UHFFFAOYSA-N 2,3-dihydro-1,3-oxazole Chemical compound C1NC=CO1 ZABMHLDQFJHDSC-UHFFFAOYSA-N 0.000 description 1
- UODFFWGYSJVFCZ-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine Chemical compound COC1=CC=NC(CCl)=C1 UODFFWGYSJVFCZ-UHFFFAOYSA-N 0.000 description 1
- PBDFBZPTRXMFBL-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=NC(CCl)=C1 PBDFBZPTRXMFBL-UHFFFAOYSA-N 0.000 description 1
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
- JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- JMHKRFZCFRFNJS-UHFFFAOYSA-N 4-chloro-n-(2-chloroethyl)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NCCCl)=CC=C1Cl JMHKRFZCFRFNJS-UHFFFAOYSA-N 0.000 description 1
- PMMVJUABCIHELF-UHFFFAOYSA-N 4-chloro-n-(2-hydroxyethyl)-3-nitrobenzamide Chemical compound OCCNC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 PMMVJUABCIHELF-UHFFFAOYSA-N 0.000 description 1
- RDENQVWOYNZEIW-UHFFFAOYSA-N 5-amino-n-(2-chloroethyl)-4-nitrothiophene-2-carboxamide Chemical compound NC=1SC(C(=O)NCCCl)=CC=1[N+]([O-])=O RDENQVWOYNZEIW-UHFFFAOYSA-N 0.000 description 1
- PHPHFQYIWLTXOG-UHFFFAOYSA-N 5-chloro-n-(2-chloroethyl)-4-nitrothiophene-2-carboxamide Chemical compound [O-][N+](=O)C=1C=C(C(=O)NCCCl)SC=1Cl PHPHFQYIWLTXOG-UHFFFAOYSA-N 0.000 description 1
- YPXQSGWOGQPLQO-UHFFFAOYSA-N 5-nitro-1,3-dihydrobenzimidazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2N=C(S)NC2=C1 YPXQSGWOGQPLQO-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- ITJOTGFGJYCEFH-UHFFFAOYSA-N ClC1=C(C=C(C(=O)NCCCl)C=C1)[N+](=O)[O-].O1CCOCC1 Chemical compound ClC1=C(C=C(C(=O)NCCCl)C=C1)[N+](=O)[O-].O1CCOCC1 ITJOTGFGJYCEFH-UHFFFAOYSA-N 0.000 description 1
- PQEAOJOEOSCHKF-UHFFFAOYSA-N ClC1=C(C=C(C=C1)C=1OCCN1)[N+](=O)[O-].O1CCOCC1 Chemical compound ClC1=C(C=C(C=C1)C=1OCCN1)[N+](=O)[O-].O1CCOCC1 PQEAOJOEOSCHKF-UHFFFAOYSA-N 0.000 description 1
- HPLOAICWWGADKD-UHFFFAOYSA-N ClC1=C(C=C(S1)C(=O)NCCCl)[N+](=O)[O-].O1CCOCC1 Chemical compound ClC1=C(C=C(S1)C(=O)NCCCl)[N+](=O)[O-].O1CCOCC1 HPLOAICWWGADKD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OXWSGQUZWFJATM-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-nitrobenzamide Chemical compound OCCNC(=O)C1=CC=CC([N+]([O-])=O)=C1 OXWSGQUZWFJATM-UHFFFAOYSA-N 0.000 description 1
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 1
- 229960000381 omeprazole Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT2437/86 | 1986-09-10 | ||
AT243786 | 1986-09-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS6377878A true JPS6377878A (ja) | 1988-04-08 |
Family
ID=3534337
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62225453A Pending JPS6377878A (ja) | 1986-09-10 | 1987-09-10 | 4、5−ジヒドロ−オキサゾ−ルの新規誘導体、その製造方法及びその使用法 |
Country Status (21)
Country | Link |
---|---|
US (1) | US4818760A (sv) |
EP (1) | EP0261478B1 (sv) |
JP (1) | JPS6377878A (sv) |
KR (1) | KR880003941A (sv) |
AT (1) | ATE62908T1 (sv) |
AU (1) | AU596869B2 (sv) |
CA (1) | CA1256109A (sv) |
CS (1) | CS268191B2 (sv) |
DD (1) | DD262230A5 (sv) |
DE (1) | DE3769563D1 (sv) |
DK (1) | DK165322C (sv) |
ES (1) | ES2028838T3 (sv) |
FI (1) | FI89267C (sv) |
GR (1) | GR3001842T3 (sv) |
HU (1) | HU198059B (sv) |
MY (1) | MY102003A (sv) |
NO (1) | NO165195C (sv) |
NZ (1) | NZ221723A (sv) |
SG (1) | SG39892G (sv) |
SU (1) | SU1574177A3 (sv) |
ZA (1) | ZA876740B (sv) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6051570A (en) * | 1997-05-30 | 2000-04-18 | Dr. Reddy's Research Foundation | Benzimidazole derivatives as antiulcer agents, process for their preparation and pharmaceutical compositions containing them |
US6852739B1 (en) | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
ATE300285T1 (de) | 1999-06-07 | 2005-08-15 | Altana Pharma Ag | Neue zubereitung und darreichungsform enthaltend einen säurelabilen protonenpumpeninhibitor |
JP4634144B2 (ja) * | 2002-08-01 | 2011-02-16 | ニコックス エスエー | ニトロソ化プロトンポンプ阻害剤、組成物および使用方法 |
CA2529984C (en) | 2003-06-26 | 2012-09-25 | Isa Odidi | Oral multi-functional pharmaceutical capsule preparations of proton pump inhibitors |
RS52233B (en) * | 2004-05-07 | 2012-10-31 | Nycomed Gmbh | THE PHARMACEUTICAL DOSAGE FORM CONTAINING GRANULES AND ITS PRODUCTION PROCEDURE |
US8394409B2 (en) | 2004-07-01 | 2013-03-12 | Intellipharmaceutics Corp. | Controlled extended drug release technology |
US10624858B2 (en) | 2004-08-23 | 2020-04-21 | Intellipharmaceutics Corp | Controlled release composition using transition coating, and method of preparing same |
US10064828B1 (en) | 2005-12-23 | 2018-09-04 | Intellipharmaceutics Corp. | Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems |
JP5457830B2 (ja) * | 2006-04-03 | 2014-04-02 | オディディ,イサ | オルガノゾル被膜を含む制御放出送達デバイス |
US10960077B2 (en) | 2006-05-12 | 2021-03-30 | Intellipharmaceutics Corp. | Abuse and alcohol resistant drug composition |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
SE8404065D0 (sv) * | 1984-08-10 | 1984-08-10 | Haessle Ab | Novel biologically active compounds |
FI861772A (fi) * | 1985-05-07 | 1986-11-08 | Chemie Linz Ag | Nya tieno(2,3-d)imidazolderivat och foerfarande for deras framstaellning. |
EP0234485B1 (de) * | 1986-02-20 | 1992-04-01 | Hoechst Aktiengesellschaft | Substituierte Thienoimidazol-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Zubereitungen und ihre Verwendung als Magensäuresekretionshemmer |
-
1987
- 1987-09-03 CA CA000546073A patent/CA1256109A/en not_active Expired
- 1987-09-04 DE DE8787112928T patent/DE3769563D1/de not_active Expired - Fee Related
- 1987-09-04 ES ES198787112928T patent/ES2028838T3/es not_active Expired - Lifetime
- 1987-09-04 AT AT87112928T patent/ATE62908T1/de not_active IP Right Cessation
- 1987-09-04 EP EP87112928A patent/EP0261478B1/de not_active Expired - Lifetime
- 1987-09-07 NO NO873722A patent/NO165195C/no unknown
- 1987-09-07 MY MYPI87001580A patent/MY102003A/en unknown
- 1987-09-08 AU AU78170/87A patent/AU596869B2/en not_active Ceased
- 1987-09-08 NZ NZ221723A patent/NZ221723A/xx unknown
- 1987-09-08 CS CS876497A patent/CS268191B2/cs unknown
- 1987-09-09 ZA ZA876740A patent/ZA876740B/xx unknown
- 1987-09-09 HU HU874022A patent/HU198059B/hu not_active IP Right Cessation
- 1987-09-09 SU SU874203301A patent/SU1574177A3/ru active
- 1987-09-09 DK DK469687A patent/DK165322C/da not_active IP Right Cessation
- 1987-09-09 US US07/094,594 patent/US4818760A/en not_active Expired - Fee Related
- 1987-09-09 KR KR870009953A patent/KR880003941A/ko not_active Application Discontinuation
- 1987-09-09 DD DD87306817A patent/DD262230A5/de not_active IP Right Cessation
- 1987-09-09 FI FI873892A patent/FI89267C/sv not_active IP Right Cessation
- 1987-09-10 JP JP62225453A patent/JPS6377878A/ja active Pending
-
1991
- 1991-04-25 GR GR90401062T patent/GR3001842T3/el unknown
-
1992
- 1992-04-11 SG SG398/92A patent/SG39892G/en unknown
Also Published As
Publication number | Publication date |
---|---|
FI89267C (sv) | 1993-09-10 |
GR3001842T3 (en) | 1992-11-23 |
DK469687A (da) | 1988-03-11 |
DD262230A5 (de) | 1988-11-23 |
ES2028838T3 (es) | 1992-07-16 |
US4818760A (en) | 1989-04-04 |
DK165322C (da) | 1993-03-29 |
FI89267B (fi) | 1993-05-31 |
CA1256109A (en) | 1989-06-20 |
AU596869B2 (en) | 1990-05-17 |
EP0261478A1 (de) | 1988-03-30 |
MY102003A (en) | 1992-02-29 |
DK469687D0 (da) | 1987-09-09 |
HUT47288A (en) | 1989-02-28 |
ATE62908T1 (de) | 1991-05-15 |
DE3769563D1 (de) | 1991-05-29 |
KR880003941A (ko) | 1988-05-31 |
NO873722L (no) | 1988-03-11 |
AU7817087A (en) | 1988-03-17 |
SU1574177A3 (ru) | 1990-06-23 |
FI873892A (fi) | 1988-03-11 |
SG39892G (en) | 1992-10-02 |
FI873892A0 (fi) | 1987-09-09 |
CS268191B2 (en) | 1990-03-14 |
NZ221723A (en) | 1989-11-28 |
ZA876740B (en) | 1988-03-14 |
CS649787A2 (en) | 1989-05-12 |
DK165322B (da) | 1992-11-09 |
NO165195B (no) | 1990-10-01 |
NO165195C (no) | 1991-01-09 |
NO873722D0 (no) | 1987-09-07 |
HU198059B (en) | 1989-07-28 |
EP0261478B1 (de) | 1991-04-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4555518A (en) | Fluoroalkoxy substituted benzimidazoles useful as gastric acid secretion inhibitors | |
US4472409A (en) | 2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion inhibiting effects | |
DK150510B (da) | Analogifremgangsmaade til fremstilling af substituerede 2-(2-benzimidazolyl)-pyridiner eller terapeutisk acceptable salte deraf | |
JP3122792B2 (ja) | 新規な活性化合物 | |
FR2720396A1 (fr) | Nouveaux N-pyridyl carboxamides et dérivés leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. | |
JPS6377878A (ja) | 4、5−ジヒドロ−オキサゾ−ルの新規誘導体、その製造方法及びその使用法 | |
EP0748317A1 (en) | Novel thiazolidin-4-one derivatives | |
JPS609716B2 (ja) | 1,2―ベンズインチアゾリン―3―オン類、それらの製造法および医薬としての使用 | |
KR900003368B1 (ko) | 신규한 인데노티아졸 유도체의 제조방법 | |
JPS63502658A (ja) | 新規な物質の組成 | |
JPS61254591A (ja) | 新規なチエノ(2、3−d)イミダゾ−ル誘導体、その製法、製剤および使用法 | |
US4678785A (en) | Thiadiazine compounds | |
CZ278281B6 (en) | ENOL ETHER OF 1,1-DIOXIDE OF 6-CHLORO-4-HYDROXY-2-METHYL-N- (2-PYRIDYL-2H-THIENO(2,3-c)-1,2-THIAZINECARBOXYLIC ACID AMIDE, PROCESS OF ITS PREPARATION AND ITS USE | |
JP2816974B2 (ja) | ベンズイミダゾール誘導体およびその製造法ならびにこれを含有する抗潰瘍剤 | |
EP0180500A1 (fr) | Dérivés de thiéno et furo - [2,3-c]pyrroles, procédés de préparation et médicaments les contenant | |
JPS61191612A (ja) | 虚血性心疾患用剤 | |
JPS59167588A (ja) | チアジアゾ−ル誘導体 | |
JPS61221175A (ja) | ベンズイミダゾ−ル誘導体およびその製造法ならびにこれを含有する抗潰瘍剤 | |
JPS6261978A (ja) | 5−フルオロ−1h−ベンズイミダゾ−ル誘導体 | |
JPS634556B2 (sv) | ||
NZ202386A (en) | Substituted 2-pyridylmethyl(thio/sulphinyl)-benzimidazole derivatives and pharmaceutical compositions | |
JPH037279A (ja) | 2―チオピランカルボチオアミド誘導体 | |
JPH0249781A (ja) | ピリジニウム誘導体 | |
JPS63250374A (ja) | 〔2−(1,3−ベンゾジオキソ−ル−5−イル)エチル〕チオ誘導体 | |
JPS63225377A (ja) | 新規テトラヒドロ−1,5−ナフチリジン誘導体およびその製造方法ならびにこれを含有する抗潰瘍剤 |